This must be a security feature that the plugin uses. My problem was the way I had the "SMTP Outgoing Server" configured.

If you're using Amazon SES as your SMTP server make sure you use "ssl://email-smtp.us-east-1.amazonaws.com:465" as your SMTP server. The "ssl://" at the beginning and the ":465" at the end are the important parts. Your server name may be different.

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